Silver-Catalyzed One-Pot Three-Component Selective Synthesis of beta-Hydroxy Selenides

A convenient, multi-component reaction of organoboronic acids, selenium powder and epoxides has been developed, providing an efficient protocol for the synthesis of beta-hydroxy selenides with excellent selectivity and good functional group tolerance. Preliminary mechanistic studies suggest that the reaction proceeds through the silver-catalyzed radical selenation of the arylboronic acids to generate a diselenide, and subsequent selenium-mediated selective ring-opening arylselenation of epoxides.